This Former Texas Cop Rode His Horse to CPAC to Say That Drugs Should Be Legalized

NATIONAL HARBOR, MARYLAND—Around the time that White House Press Secretary Sean Spicer revealed that the Trump administration might crack down on recreational weed, a man in a cowboy hat and a shirt reading "Cops Say Legalize Drugs" was strolling through the halls of the Gaylord National Resort & Convention Center. Howard "Cowboy" Wooldridge, a former detective who now lobbies on behalf of universal drug legalization with Law Enforcement Against Prohibition (LEAP), is a bit of a CPAC celebrity. He doesn't just buck the navy-suit uniform; he bucks the other law enforcement organizations that are among the most powerful interests gathered here—and who are, for the most part, adamantly opposed to legalization. This is his twelfth straight conservative Woodstock, and the environment is the least friendly it's been in years. He thinks the argument should be over by now.

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"The government will tell you the last survey showed 900,000 teenagers are employed selling drugs off sidewalks. Twenty of them are shot everyday. That's immoral, wrong, and preventable—no kid has a job selling beer off the sidewalk."

Wooldridge still has a bit of a twang from his Texas days. That's where he started this campaign in 1997 when, as he says, "the wind was coming at me like a Class-2 hurricane." He twice rode his horse, Misty, across America to bring attention to the cause (he claims Misty is tied up behind the convention center and sends me a photo later in the day). Along those trips, people threatened to shoot him off his saddle, and he jokes he needed a bulletproof vest for his first two CPACs. But a few years back, things began to change.

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Howard Wooldridge

"In 2006 or 2007, when Ron Paul came on, he flipped all the college kids to being a little libertarian, and ever since then the young people here have been wonderful. I get handshakes, I get selfies. There's been a permanent shift."

Yet this year's environment is far less hospitable to the reformer types. President Trump has spoken on the heroin epidemic, but he also grew fond of "law and order" through the campaign. Then, he picked Jefferson Beauregard Sessions to serve as his attorney general, a hardliner on marijuana who is also a reliable friend to the private prison industry. Wooldridge calls that special interest his "third biggest adversary on Capitol Hill," because "their business model depends on having 2.3 million people in prison, and they prefer 3.3 million." The number one, remember, is other police organizations. The second?

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"Big Pharma doesn't like this," he says. "They don't want you to grow your own medicine in your backyard for free."

"Their business model depends on having 2.3 million people in prison."

Those obstacles have always been formidable. "You cannot compete with the drug companies," Wooldridge says, "They have more money than God." What's new is the shrinking influence of the Republican Party's mythical libertarian streak. Whereas one of the Pauls—Ron or Rand—won five of the last seven straw polls at CPAC, we have entered the age of Trump. There are no Pauls this year, and the libertarian groups have largely faded to the background. To the extent real small-government principles have ever dictated Republican policy when the party's in power, those days are likely over. And while there might be a new brand of conservatism afoot (or at least a new Republican coalition) whose leader crafted it by bucking convention, there is no room here for disagreement with Supreme Leader.

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Wooldridge remains undeterred.

"I know Jeff Sessions and his views. I'm an inside-the-Beltway kind of guy. My 47 cents is that Trump is going to say, 'What's important to my base? Immigration, jobs, heroin abuse and overdoses—over 30,000 last year. I think he'll tell Sessions to work on those, get the wall going, but do a better job on heroin by not wasting time going after marijuana shops in Colorado."

Howard Wooldridge

(Wooldridge, like cartel expert Don Winslow, does not think The Wall will prevent drug trafficking. "This is nonsense," he says, citing tunnels and the emerging use of drones. "He really has become a politician.")

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For all the cowboy hats and horses, though, Wooldridge has adapted well to the rhythms of Beltway life. He moved up to D.C. to lobby Congress full time, and has picked up a bit of northeast, big-city urgency. He is rapid fire as he explains that the money and manpower required for the Drug War could be put to far better use.

"We got pedophiles all over the chartrooms, all over social media, and we're still chasing Charlie Sheen. And for what? To get him in rehab? Federal agents who could be focused on the Orlandos and San Bernadinos are chasing green plants and white powders to absolutely zero-point-zero impact on the situation. This whole thing has been a trillion dollar failure. It's Prohibition, part two."

"You cannot compete with the drug companies. They have more money than God."

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Two college-age CPACers sidle up. Aron Winburn, a Coastal Carolina student, announces himself immediately as a libertarian—and says he loves the shirt.

"I'm for delegalization in the sense it will clean up our judicial system to focus on people who commit violent crimes, and will hurt the drug cartels," Winburn says.

"Exactly right," nods Wooldridge.

"The black market will always address these demands," Winburn adds of banned substances.

"Exactly," Wooldridge responds. "When I got drunk at 16—and don't do drugs kids—but I bought the beer from who? My brother. My older brother, I gave him money for a six pack..."

Wooldridge believes if he goes person-by-person long enough, things will pile up. He says that's what happened in Florida, where 71 percent of voters backed a ballot initiative legalizing medical marijuana in November despite huge opposition from familiar constituencies. For those less receptive than Winburn, including Republicans in Congress, he likes to talk to them just enough to give them something to chew on when they leave. Sometimes, he'll simply ask them for one clear benefit of drug prohibition.

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